Michelle Obama served as the First Lady of the United States, entering the White House alongside Barack Obama. In this candid conversation, she joins Steven with her brother Craig Robinson, a former college basketball coach turned executive, to open up about everything from Trump’s inauguration to marriage challenges, grief, and rediscovering her purpose. Together, they discuss: * How their parents instilled empathy, discipline, and resilience growing up amid racial tension. * Michelle’s journey through elite schools and corporate law, driven by a need to tick society’s boxes. * The evolution of Michelle and Barack’s relationship, from colleagues to lifelong partners. * Fertility struggles, parenting tips, and what it really takes to sustain a long-term marriage. * Navigating life in the White House, grief, personal boundaries, and rediscovering her true calling. 00:00 Intro 02:01 Michelle and Craig's Childhood 04:38 Values Learned from Their Parents 08:35 Michelle Skipping Second Grade 12:06 The Role of Race in Their Childhood 15:09 What "White Flight" Means 16:50 Coping with Racism 20:45 Overcoming Being Underestimated 26:23 Michelle's Search for Identity 30:10 Meeting Barack 31:49 Introducing Barack to the Family 33:38 Why Michelle Initially Rejected Barack 37:18 Michelle's Career Change: Pursuing Joy 40:41 Relationship with Barack 44:46 Couples Counseling with Barack 49:23 Pregnancy Struggles 56:16 Hardest Moments in Their Marriage 57:20 Barack Obama Runs for Public Office 01:03:18 What I Should Have Said to Barack 01:07:00 Being the First Black First Lady and Facing Scrutiny 01:15:06 Remembering Your Mother 01:16:42 The Death of Your Mother 01:18:25 Processing the Grief 01:20:31 Not Attending Trump’s Inauguration Listen to Michelle & Craig's new podcast IMO: ⁠https://bit.ly/3YnxIUg Follow Michelle: Instagram - https://bit.ly/3Ymxs7W Twitter - https://bit.ly/4cYXiVC Follow Craig: Instagram - https://bit.ly/4lThkVB Twitter - https://bit.ly/4lTGJ1f YouTube: You can purchase Michelle’s book, ‘Overcoming: A Workbook’, here: https://amzn.to/4jTqcsi (UK) / https://amzn.to/3SbbelM (US) Think like a CEO - join the 100 CEOs newsletter: https://bit.ly/100-ceos-newsletter The 1% Diary is back - limited time only: https://rebrand.ly/r0ogao4 The Diary Of A CEO Conversation Cards (Second Edition): https://g2ul0.app.link/f31dsUttKKb Get email updates: https://bit.ly/diary-of-a-ceo-yt Follow Steven: https://g2ul0.app.link/gnGqL4IsKKb Sponsors: Airalo - https://try.airalo.com/TheDiaryOfACEO with code DOAC3 Vivobarefoot - https://vivobarefoot.com/DOAC with code DIARY20 for 20% off